For Sale
Single family home for sale at 349 Old Stockbridge Rd, Lenox, MA 01240 | MLS# 73567764 | Listing updated on 2026-09-08
Photo 1 of Single family home for sale at 349 Old Stockbridge Rd, Lenox, MA 01240 | MLS# 73567764 | Listing updated on 2026-09-08
Photo 2 of Single family home for sale at 349 Old Stockbridge Rd, Lenox, MA 01240 | MLS# 73567764 | Listing updated on 2026-09-08
Photo 3 of Single family home for sale at 349 Old Stockbridge Rd, Lenox, MA 01240 | MLS# 73567764 | Listing updated on 2026-09-08
Photo 4 of Single family home for sale at 349 Old Stockbridge Rd, Lenox, MA 01240 | MLS# 73567764 | Listing updated on 2026-09-08
38+
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Street View

$2,295,000

Monthly Est:$11,423

  • Beds Icon31 Beds
  • Beds Icon
    29 Baths
  • Beds Icon38,415sqft

349 Old Stockbridge Rd, Lenox, MA 01240

$11,423/moEst:

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  • Single Family Residence

  • Built in 1903

  • $-- HOA

  • 11.9 acres lot

  • $60/sq.ft

Description

A singular opportunity to reimagine one of Lenox's historic Berkshire estates. Set on 11.90± acres just minutes from downtown Lenox and the cultural attractions of the Berkshires, Overlee was built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan/Jacobean Revival style.The original mansion remains at the heart of the property, surrounded by broad lawns and buildings added during its later evolution into an educational campus. Much of the character of the original country house remains, including handsome woodwork, substantial fireplaces, gracious rooms, and a beautiful ballroom. Most recently used for classrooms and administrative functions, the mansion was originally designed as a residence, with bedrooms on its upper floors.Beyond the main house are two dormitory residences with approximately 24 bedrooms and shared common spaces, a separate multi-level building with commercial kitchen and dining facilities, classrooms, offices, library, conference and infirmary spaces, a substantial gymnasium, and additional support buildings. For a residential buyer, this unusual collection offers possibilities for guest and staff accommodations, studios, offices, recreation, wellness, or a multi-generational Berkshire estate, subject to applicable approvals.The gymnasium could accommodate fitness, indoor tennis, pickleball, squash, or other private amenities. Existing infrastructure includes public water, multiple electrical services, mixed heating systems, central air in the dormitories and gymnasium, commercial sprinklering in select buildings, extensive parking, and established internal circulation.Hillcrest currently operates on the campus under a lease through June 2027 and presently anticipates vacating in February/March 2027.This offering is for 349 Old Stockbridge Road only. The property is also marketed as part of a combined offering with 40 Frothingham Crossing; see MLS #73518284.For its next steward, Overlee offers the rare chance to inherit not simply a house, but an entire Berkshire estate—historic architecture, expansive grounds, and a collection of buildings ready to support a new vision.Offered at $2,295,000.

  • Houzeo last checked: 54 minutes ago
  • Listing updated: September 8, 2026 at 6:37 pm
  • Listing Provided by: Selina Lamb (413) 329-0435 | Birch Properties (413) 613-4363
  • Source: MLS Property Information Network-MA | MLS#: 73567764 MLS Property Information Network-MA

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Berkshire County

  • City

    Lenox

  • Neighborhood

    --

  • Year Built

    1903

  • HOA Fees

    -

  • Finished Area

    38,415 sqft

  • Lot Size

    11.9 acres lot

  • Basement Area

    - sqft

  • MLS Name

    MLS Property Information Network

  • MLS Number

    73567764

  • MLS Status

    Active

  • Days on Market

    61

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 31

    Bathrooms: 29

Interior

  • Exterior Features

    Patio, Pool Inground, Storage, Sprinkler System

  • Sewer

    Private Sewer

  • Appliances

    Electric Water Heater, Dishwasher, Microwave, Indoor Grill, Refrigerator, Freezer, Washer, Dryer, Range Hood

  • Heating

    Central, Forced Air, Oil

  • Flooring

    Wood, Tile, Carpet, Laminate

  • Cooling

    Central Air, Wall Unit(s), Ductless

Construction

  • Year Built

    Year Built: 1903

  • Home type

    Single Family Residence

  • Construction Materials

    Frame, Brick

  • Foundation Details

    Stone

  • Architectural Style

    Victorian, Mid Century Modern

  • Roof

    Metal, Asphalt/composition Shingles

Utilities & Energy

  • Pool Features

    In Ground

  • Water Source

    Public

  • Basement

    Walk Out Access, Interior Entry, Concrete

  • Electric

    100 Amp Service, 200+ Amp Service

  • Parking Features

    Detached, Paved Drive, Off Street, Paved, Unpaved

Other Features

  • Disclosures

    This Listing Does Not Include Property At 40 Frothingham Crossing, Lenox.

  • Patio And Porch Features

    Patio

  • Lot Features

    Underground Storage Tank

Price History

DateEventPrice

08/25/2026

Source: mls_logoMLS Property Information Network-MA #73518283

Price Increased

$3,195,000 +39.22%

$0/sqft

08/25/2026

Source: mls_logoMLS Property Information Network-MA #73567764

Price Decreased

$2,295,000 -38.80%

$0/sqft

07/20/2026

Source: mls_logoMLS Property Information Network-MA #73518283

Listed for Sale

$3,750,000

$0/sqft

06/16/2026

Source: mls_logoMLS Property Information Network-MA #73518283

Pending

$3,750,000

$0/sqft

Based on information provided to and compiled by MLS Property Information Network, Inc. covering through Oct 26, 2026, 07:14AM. The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third-party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified. © 2026 MLS Property Information Network, Inc. All Rights Reserved.

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